Cherokee Park Homes for Sale

Located just two and a half miles south of downtown Sarasota, Cherokee Park is a highly sought after "West of Trail" neighborhood, offering a charming, quiet retreat from Sarasota's bustling city center. What started as a 1920s dreamscape that was stalled by the Great Depression, Cherokee Park really took off after World War II, when mid-century ranch-style and Spanish-style homes filled the community. Today, the neighborhood boasts a variety of architectural styles with unique, high-end updated interiors, all paying homage to the charming neighborhood in which the residences stand. A product of the original 1920s dreamscape, the community is still separated by a beautiful stucco wall and ornate entrance, leading to an enclave of mansions and mid-century homes nestled among palm-lined streets. Read More About Cherokee Park.

5 Properties Found.
Sort By:

Cherokee Park Real Estate

The highly sought after neighborhood of Cherokee Park serves as home to a diverse resident population, including young professionals, families, retirees, and many of the doctors and other medical staff at nearby Sarasota Hospital. Homeowners enjoy steadily rising home prices, with home values increasing at a rate well above the national average. The neighborhood's assigned elementary school, Southside Elementary, sits just outside the northeast corner of the neighborhood and routinely receives top ratings among Florida's public schools. 

The community's diverse population can easily be explained by the multitude of activities and cultural outlets within a short drive of the quiet retreat, providing a wide range of entertainment options for resident of all ages and interests. Cherokee Park provides convenient access to high-end shopping, with a variety of shops at nearby Westfield Southgate Mall. For food lovers, the community is just a short drive from Southside Village, where many of the Sarasota's top-rated restaurants are located. Residents also boast about the nearby thriving art and cultural scenes, with year-round theater events, art showcases, charity galas, and even a widely-popular ten-day film festival. 

While the conveniences of downtown living are certainly a reason for Cherokee Park's desirability, perhaps most highly prized about the community is its convenient access to beautiful Siesta Key. Siesta Beach at Siesta Key is just one of Sarasota's many award winning white sand beaches. A natural product of the Mississippi River Delta, the beautiful white sand along Sarasota's beaches consists of ninety percent quartz, providing for cool, soft sandy beaches that bring visitors and locals back again and again. With a gorgeous landscape and a multitude of convenient entertainment options, it is no wonder why Cherokee Park is regularly one of Sarasota's most highly sought-after residential communities.

From Our Blog - West of Trail
Rising Inventories - Market Shifting in Sarasota?

Is this the end of a boom cycle in the real estate market? It is too early to tell but some believe so. Below I provided graphs of inventories levels in Sarasota, Manatee, Longboat Key, Siesta Key, ... Read more

4907 Eastchester Drive - Very Cool House!

I was poking through MLS and found this really great looking home for sale west of the trail in the Museum area of Sarasota. I thought you might enjoy the photos below. Give us a call at 941.822.... Read more

The Hottest Neighborhood in Sarasota?

If you’re looking for luxury with a rich history, established neighborhoods, and an elegant mix of old-world glamour and modern sophistication, living West of the Trail in Sarasota is the ... Read more

Mid Century Modern For Sale

You have to check out this fabulous mid-century modern home for sale in Oyster Bay Estates. I was poking around the MLS this morning and noticed it. This lovely home at 1833 N Lakeshore Drive just ... Read more